Preheat your oven to 400 degrees. Line a cookie sheet with tinfoil and place a cooling rack on top of it,
Stir together ALL of the sauce ingredients in a medium pot and bring to a boil on high heat. Once boiling, cook for 1.5 minutes, stirring frequently.
Once the sauce has boiled for 1.5 minutes, turn the heat down to medium and simmer until the sauce begins to thicken and reduce, about 9-10 minutes, stirring frequently.
Once reduced, pour the sauce into a high powered blender, or small food processor, and blend until smooth. Transfer to a measuring cup (you should have about 6 ounces.)
Pour the drained pineapple onto a layer of paper towel. Use another paper towel to gently press out excess moisture.
Cut all the bacon slices in half vertically. Then wrap half a slice around each pineapple - you can hold in some slices of bacon if they are super thick, but they shrink A LOT once cooking. Place the wrapped pineapple onto the cooling rack on top of the cookie sheet. You'll need to pack them together tightly to fit them all on. I also recommend putting them wrapped-side-down so that the bacon sticks to itself.
Bake until the bacon is nice and crispy and golden brown, about 37-40 mins. Reduce the heat to 375 degrees.
Rub ALL of the sauce over top of the bites, making sure you spread it on nice and thick.
Bake until the sauce is thick and cooked, but still a little bit "goopy", about 15 minutes.
Throw in some toothpicks and DEVOUR!